Transamidation of Primary Amides with Amines Using Hydroxylamine Hydrochloride as an Inorganic Catalyst

Metal-free catalysis: A method for the transamidation of primary amides with primary or secondary amines provides access to secondary and tertiary amides, by utilizing catalytic quantities of hydroxylamine hydrochloride to activate the chemically robust primary amide group (see scheme). A mechanism of primary amide activation through a hydrogen-bonding complex is proposed.